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Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)(5) and Phenanthroline System
- Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)(5) and Phenanthroline System
- Hwang, Joon Young; Baek, Jong Hwa; Shin, Tae Il; Shin, Jung Ha; Oh, Jae Won; Kim, Kwang Pyo; You, Youngmin; Kang, Eun Joo
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ORGANIC LETTERS
- ORGANIC LETTERS vol. 18, no. 19, pp. 4900 - 4903
- AMER CHEMICAL SOC
- SCI; SCIE; SCOPUS
- Document Type
- An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)(5)] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)(5), 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.
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